You’re probably using AI for onboarding all wrong. I was too. Here’s the painful story of how I learned to do it right.
I’ve managed over $2M in remote team payroll. I’ve built and sold two companies, RemoteTeam to Gusto and MovieLaLa to Gfycat. I’ve invested in over 200 companies, including some of the biggest names in AI like Anthropic, OpenAI, and Scale AI. And I’ve seen every AI onboarding mistake in the book.
The hype around AI in HR is deafening. Everyone is scrambling to automate everything. And onboarding is the low-hanging fruit. Or so it seems.
I get it. The promise of a perfectly automated, scalable, and efficient onboarding process is seductive. A world where new hires are seamlessly integrated into the company culture and workflow, all with the magic of AI. No more repetitive tasks for your HR team. No more new hires feeling lost and overwhelmed. It sounds like a dream.
But here’s the hot take: for most companies, especially startups, this is a dangerous fantasy. Chasing the AI onboarding dream is not just a waste of time and money; it’s actively harming your company.
The Painful Truth About AI Onboarding
I learned this the hard way. At RemoteTeam, we were obsessed with efficiency. We were building tools for remote teams, so we had to be the best at it ourselves. We tried to automate everything, including onboarding. We built a beautiful, automated system. New hires would get a series of emails, access to a personalized dashboard, and a chatbot to answer their questions. It was a work of art.
And it was a complete failure.
Our new hires were going through the motions, but they weren’t connecting. They weren’t building relationships. They weren’t understanding the nuances of our culture. They were just checking boxes. And it showed in their work. We had a retention problem, and I couldn’t figure out why. We were doing everything by the book. The “AI-powered future of work” book, that is.
The breaking point came when we hired a brilliant engineer from Brazil. He was a rockstar. On paper, he was the perfect fit. He went through our automated onboarding process without a hitch. He told us he was excited to be there. And then, three weeks later, he quit.
I was floored. I called him to understand what went wrong. His answer was a punch to the gut. “I never felt like I was part of a team,” he said. “I felt like I was interacting with a machine.”
That’s when I realized: we had automated the humanity out of our onboarding.
The Human Connection: The Most Important Metric You're Not Tracking
That conversation was a wake-up call. I realized that in our quest for efficiency, we had forgotten the most important thing: human connection. We were so focused on the “what” of onboarding – the paperwork, the training, the tools – that we had completely neglected the “who.”
Think about it. When you join a new company, what do you remember most? The slick onboarding portal? The automated email sequence? Or the people? The conversations you had? The feeling of being welcomed into a new community?
No amount of AI can replicate the feeling of a genuine human connection. No chatbot can replace a manager who takes the time to get to know you. No automated workflow can substitute for a team that makes you feel like you belong.
This isn’t just a feel-good platitude. It’s a business imperative. A study by Gallup found that employees who have a best friend at work are seven times more likely to be engaged in their jobs. And engaged employees are more productive, more innovative, and less likely to leave.
So, what’s the alternative? How do you create an onboarding process that is both efficient and human-centric? Here’s what we did at RemoteTeam, and what I advise all the companies I invest in to do.
The “Do This Instead” Onboarding Playbook
1. The Pre-Onboarding Buddy System
Before a new hire’s first day, we assign them an “onboarding buddy.” This isn’t their manager. It’s a peer from their team who has been at the company for a while. The buddy’s job is simple: to be a friendly face and a resource for the new hire.
They reach out a week before the start date, just to say hi and answer any questions. They schedule a virtual coffee chat on the first day. They check in regularly during the first few weeks. This simple act of human connection makes a world of difference. It immediately makes the new hire feel like they are part of the team, not just another cog in the machine.
2. The “First Week” Deep Dive
The first week is not about overwhelming the new hire with information. It’s about immersion. We schedule a series of one-on-one meetings with key people across the company. Not just their direct team, but people from other departments as well. The goal is for the new hire to understand the big picture, and to start building relationships from day one.
We also have a “founder’s chat.” I personally sit down with every new hire for 30 minutes. I tell them my story. I tell them the story of the company. I answer their questions. This is not scalable. And that’s the point. It shows that we value our people, and that we are all in this together.
3. Use AI as a Super-Powered Assistant, Not a Replacement
I’m not saying you should ditch AI altogether. That would be foolish. AI is an incredibly powerful tool. But it should be used to augment, not replace, human interaction.
We use AI to handle the tedious, administrative tasks. The paperwork. The compliance training. The IT setup. This frees up our HR team to focus on what they do best: building relationships and creating a great employee experience.
We also use AI to personalize the onboarding experience. For example, we use a tool that analyzes a new hire’s personality and communication style, and then provides their manager with a “user manual” on how to best work with them. This is a great example of using AI to enhance human connection, not replace it.
The Bottom Line
Stop chasing the shiny new toy. Stop trying to automate everything. Instead, focus on what really matters: human connection.
Build an onboarding process that is personal, relational, and human-centric. Use AI as a tool to help you do that, not as a crutch to avoid it. Your new hires will thank you for it. And your bottom line will too.
I’ve seen this work time and time again. At RemoteTeam, our retention rate skyrocketed after we implemented this new approach. And the companies I’ve invested in have seen similar results. So, before you go all-in on AI onboarding, take a step back and ask yourself: are you automating the humanity out of your company?
Frequently Asked Questions
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.